Furfuryl alcohol-derived bifunctional furan epoxy and method for producing same

Abstract

A method for producing bifunctional furan epoxy (BFFE) according to various embodiments of the present disclosure uses a bio-based monofunctional furan raw material to produce BFFE, and may include synthesizing BFFE raw material by reacting furfuryl alcohol, formaldehyde, and an acid-base mixture catalyst, and polymerizing BFFE by adding epichlorohydrin (ECH), a base catalyst, and a solvent to the BFFE raw material.

What is claimed is: 
     
       1. A method for producing bifunctional furan epoxy (BFFE), the method using a bio-based monofunctional furan raw material to produce BFFE, and the method comprising:
 synthesizing BFFE raw material by reacting furfuryl alcohol, formaldehyde, and an acid-base mixture catalyst; and 
 polymerizing BFFE by adding epichlorohydrin (ECH), a base catalyst, and a solvent to the BFFE raw material, 
 wherein the solvent comprises one or more solvents selected from a group consisting of ether based alcohols comprising ethylene glycol methyl ether, propylene glycol methyl ether (PGME), and butylene glycol methyl ether. 
 
     
     
       2. The method of  claim 1 , wherein the formaldehyde is liquid formaldehyde. 
     
     
       3. The method of  claim 2 , wherein the liquid formaldehyde comprises formalin. 
     
     
       4. The method of  claim 1 , wherein the acid-base mixture catalyst is a mixture of an organic acid and a conjugate base of the organic acid. 
     
     
       5. The method of  claim 2 , wherein the organic acid is an organic acid having a carboxylic group, comprising one or more selected from a group consisting of acetic acid, acetoacetic acid, adipic acid, azelaic acid, n-butyric acid, benzoic acid, citric acid, cyclohexanecarboxylic acid, enolpyruvic acid, formic acid, fumaric acid, galactaric acid, galactonic acid, glucaric acid, gluconic acid, glutaric acid, glyceric acid, glyceric acid 2-phosphate, glycolic acid, glyoxylic acid, hydroxybutyric acid, n-hexanoic acid, isobutyric acid, isophthalic acid, itaconic acid, lactic acid, levulinic acid, malic acid, methyl malonic acid, n-pentanonic acid, pimelic acid, propionic acid, succinic acid, suberic acid, tartaric acid, and terephthalic acid, used alone or in combination. 
     
     
       6. The method of  claim 1 , wherein the base catalyst comprises one or more selected from a group consisting of sodium hydroxide (NaOH), potassium hydroxide (KOH), calcium hydroxide (Ca(OH)) 2 ), ammonium hydroxide (NH 4 OH), and magnesium hydroxide (Mg(OH) 2 ), used alone or in combination. 
     
     
       7. The method of  claim 1 , wherein in the polymerizing the BFFE, an epoxy of the following Formula 1 and an epoxy of the following Formula 2 are obtained: 
       
         
           
           
               
               
           
         
         wherein n≥0 and m≥1. 
       
     
     
       8. The method of  claim 7 , wherein the BFFE comprises:
 a monomeric component wherein n=0 in Formula 1 or m=1 in Formula 2; and 
 a polymeric component wherein n>0 in Formula 1 and m>1 in Formula 2, 
 wherein the monomeric component is obtained in a yield of 50% or more, and formation of the polymeric component is suppressed. 
 
     
     
       9. The method of  claim 1 , wherein the reaction is performed as a one pot reaction. 
     
     
       10. Bifunctional furan epoxy (BFFE) produced according to the method of  claim 1 . 
     
     
       11. A method for producing bifunctional furan epoxy (BFFE), the method using a bio-based monofunctional furan raw material to produce BFFE, and the method comprising:
 synthesizing BFFE raw material by reacting furfuryl alcohol, formaldehyde, and an acid-base mixture catalyst; and 
 polymerizing BFFE by adding epichlorohydrin (ECH), a base catalyst, and a solvent to the BFFE raw material, 
 wherein the polymerizing the BFFE comprises:
 conducting a first reaction by adding ECH, a base catalyst, and a solvent to the BFFE raw material; and 
 conducting a second reaction by reducing reaction system pressure and then additionally adding the base catalyst.